Water → HCID 68796301, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(3,5-dimethoxy-4-i-propylphenyl)-1,3-diphenylpropan-2-ol (0.63 g, 1.6 mmol) in CH2Cl2 (10 mL) at −78° C. under N2 was added BBr3 (1M in CH2Cl2, 5.0 mL, 5.0 mmol) dropwise. After the reaction was stirred at −78° C. for 1 h, the temperature was allowed to rise to room temperature and the reaction mixture was stirred at room temperature over night. Water (50 mL) was added followed by 20% NaOH to adjust pH>12. The organic layer was removed and the aqueous layer was washed with hexane (2×10 mL). The aqueous layer was acidified with 6N HCl to pH 1 and extracted with ether (3×50 mL). The extract was washed with water (10 mL) and brine (10 mL) and dried over anhydrous Na2SO4. Evaporation of ether followed by flash chromatography using ethyl acetate:hexane (1:9) gave 5-(1-benzyl-2-phenylethenyl)-2-i-propyl-1,3-benzenediol (1).(0.26 g, 47%) as a liquid, which solidified on standing at 0° C. 1HNMR (CDCl3, ppm): δ 1.38 (d, J=7.1 Hz, 6H), 3.52 (hept, J=7.1 Hz, 1H), 4.08 (s, 2H), 6.51 (s, 2H), 7.13 (s, 1H), 7.2-7.4 (m, 10H).

Provenance & Evidence